


Yo Hoe! Gosh Dangit I Want A Pirates Life For Me

by Bobgod1234



Category: Once Upon a Time (TV)
Genre: Anal Fingering, Anal Fisting, Anal Sex, Blow Jobs, Family Incest, Father-Son Relationship, First Time Blow Jobs, Gay Love, Gay Sex, Grandparent/Grandchild Incest, Hardcore, Loss of Virginity, M/M, Making Out, Nipple Play, Public Sex, Step-Dad & Son Incest, eating ass, hair fetish
Language: English
Status: In-Progress
Published: 2017-06-05
Updated: 2017-06-05
Packaged: 2018-10-31 10:35:00
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 4,881
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10897560
Author URL: https://archiveofourown.org/users/Bobgod1234/pseuds/Bobgod1234
Summary: Now that the final battle was over, Henry could finally start thinking about his future, and who he was as a person. He realized that without his sudden lust for heroism, he no longer felt a need to date Violet. He decided to look elsewhere for love, somewhere closer than he thought. After Emma and Hook left to Vegas to celebrate their honeymoon, Henry went to live with David for two weeks. During the short time that Henry had lived with David before, he'd had some time to get a true male influence. Henry had to admit that David was the sexiest person alive. It actually turned him on more that he was his Grandpa. Snow was at work teaching all day, while Belle took care of Gideon and Neal so that David could make sure that teenage Henry didn't get into any trouble. As the days went by, they got really close, and Henry fell in love with him. This takes place after season 6.





	1. Please Grandpa, be my Daddy.

**Author's Note:**

  * For [To all fans that have been waiting for Henry to finally have gay sex with someone besides Peter Pan](https://archiveofourown.org/gifts?recipient=To+all+fans+that+have+been+waiting+for+Henry+to+finally+have+gay+sex+with+someone+besides+Peter+Pan).

**Summary for the Chapter:**

> Now that the final battle was over, Henry could finally start thinking about his future, and who he was as a person. He realized that without his sudden lust for heroism, he no longer felt a need to date Violet. He decided to look elsewhere for love, somewhere closer than he thought. After Emma and Hook left to Vegas to celebrate their honeymoon, Henry went to live with David for two weeks. During the short time that Henry had lived with David before, he'd had some time to get a true male influence. Henry had to admit that David was the sexiest person alive. It actually turned him on more that he was his Grandpa. Snow was at work teaching all day, while Belle took care of Gideon and Neal so that David could make sure that teenage Henry didn't get into any trouble. As the days went by, they got really close, and Henry fell in love with him. This takes place after season 6.

David decided one day that Henry should really experience nature for himself. After all, Henry always spent his days trapped in a house or school, and when he was exploring the woods, it was always for a mission to stop evil. David wanted Henry to learn that not everything had to be about keeping the light alive or stopping the darkness, and that now that the final battle was over; that he could finally relax and live his life for himself. So, David decided to take Henry to the beach. "Hey Henry, I thought maybe you and I could go to the beach and just hangout?" "Yeah that'll be fun!" Henry got dressed and headed outside to get in the truck. He got in and then they drove off. They got to the beach and they set up a little area for themselves. The good thing about being in a small town was that it was pact and you had privacy. They were the only people at the beach so it was pretty nice. Henry sat down on the sand and started to apply sunscreen on his legs. David stood up in front of him and unbuckled his belt and took off his pants. He had on a pair of tight black swim trunks that made his dick looked huge in his shorts. David took off his shirt and revealed his ripped six pack. Henry couldn't stop staring at his amazing body. His chest was huge with the sexiest shade of pale white skin. He had that Vline on him that made him extremely weak. "Henry are you ok?" "What yeah I'm fine" Henry was staring at him. David got into the water and went under. Henry took off his shirt and pants. He got in the water and started to swim and looked for David but couldn't find him. He felt two hands around his waist and he started to panic. Then David came up and started to laugh and Henry realized it was just him. "Gosh Grandpa you scared me" he said. David put his mouth to Henry's ear and whispered. "Sorry." It made Henry hard in his shorts, and to make things worse, he could feel David's dick against his ass. They continued to play in the water for a long time. They were having such an amazing time that they just continued to laugh and play, and they forgot everything that was bad in the world. They sat on the beach and just talked and looked out at the fading sun in the distance. Henry sat and stared at his beautiful Grandpa and the bulge in his shorts. Henry grew hard, which was very hard to hide. "Henry it looks like you're a little excited there. Are you okay?" "What? Oh gosh I'm sorry" "Henry its fine. It's completely normal, but I couldn't help but noticed your looks towards me." Henry didn't know what took over him but before he could say anything Henry leaned in and kissed David on the lips. To Henry's surprise David didn't pull away at first, but then he separated it and said. "Henry you're my Grandson we shouldn't be doing this" "Why not. Why shouldn't we?" "Because it's not right" "Come on let's just have some fun no one has to know" "Alright fine but this is between me and you and your lucky I haven't had sex in almost 3 months" David said then winked. They kissed each other passionately and David pulled Henry on his lap. Henry felt David's bulge on his ass which made him very hard. David went and laid Henry on his back and started to kiss lower and lower. Daivd took off his pants and Henry's dick sprang up. David started to stroke his dick slowly which made Henry moan uncontrollably. "You're still a virgin aren't you?" "How did you know?" "Because I haven't even sucked you yet and you're already moaning like crazy" he said. David took his dick into his mouth which made Henry moan louder. It felt so amazing that Henry couldn't even describe how it felt. David's mouth was warm and soft. His tongue kept going all over Henry's dick, and it felt out-of-this-world amazing. Henry felt like his dick was going to explode and he just could not stop moaning with pleasure. Henry felt himself getting close, but this time it felt so much more powerful than it ever had before when he masturbated. "I'm gonna cum Grandpa!" Henry moaned. Then he shot his load deep into David's throat. Henry sat down for a while to try and catch his breath. Then he sat up and threw Daivd on his back "I want to return the favor" Henry took off David's boxers and his cock came popping out, oozing with pre-cum. "Wow so eager I like that! Ok Henry. All you do is" before he could even finish Henry took his dick into his mouth and started to suck fast. David moaned loud and sat up and put his hand on Henry's head. "I'm sorry am I doing it wrong?" "NO you're FUCKING AMAZING at thiS. KEEP GOING!" Henry took him back into his mouth and continued to suck. His dick tasted very salty but Henry's was leaking with pre cum. Henry's jaw started to hurt but he didn't want to stop sucking him. "Henry Im Close I'm gonna cum" Henry didn't stop for one second until David shot his load in his throat and he swallowed it all. It was sweet tasting and a little salty. "I'm not going to lie to you Henry your grandmother is nowhere near as good as you" "I want you to fuck me!" "Are you sure Henry?" "Yes please I want you inside me. I want you to be my first time Grandpa" "Alright it's going to hurt at first but then it will get better. Get on your back" Henry got on his back and lifted his legs into the air. David got in back of him and inserted a finger inside of him. It hurt Henry a little bit, but the more David moved himself around in him it felt better. He stuck another finger inside him which made Henry feel even better. David took them out and then put the head of his dick against Henry hole. He slowly inserted into Henry all the way. "Ow Grandpa this hurts" "It'll be better I promise" he slowly started to move trying to get his hole use to his dick. Henry grabbed onto the towel and moaned as he slowly thrusted into him. "Go faster Grandpa!" it started to feel better. The pain was replaced with pleasure. He started to go faster and faster which brought more pleasure until there was no longer pain, but knee-buckling pleasure. "GO fast grandpa" as soon as Henry told David that, he thrusted his dick deep and hard inside of him. It felt amazing and Henry couldn't think it could get any better until something happened. Henry felt like he was hit with a wall of pleasure which made him moan loud. "OH GRANDPA HIT ME RIGHT THERE!" Henry dug his nails into David's back as the rammed his dick into him. "OH Henry your ass is sooo tight!" "It feels so good I have to cum!" Henry shot his load onto David's abs and his stomach. "I'm gonna cum Henry!" He moaned and gave Henry a facial. Then they made out for a while and went in the water to get cleaned up. Finally they got dressed and headed back to the town.


	2. Comfort of a Hairy Pirate

A few weeks later, Emma and Hook came back from their real honeymoon. Henry was sad when he heard the news because this meant he wouldn't get to see his grandpa, as much. But he was excited to see his mom and step-dad again. Mmm Daddy..... Henry would definitely get used to saying that. "No" Henry thought to himself. "I'm not going to become a man-whore like Regina." A couple of days passed by after they returned. Everything had gone back to 'normal' and it was finally starting to feel like they were living their happily ever after. Since they did indeed live in Storybrooke in the real world, every student got Memorial Day off. Hook decided to take the day off as Co-Sheriff to take Henry sailing. Henry was so relaxed staring down at the water as the ship cut through the waves. He truly understood why Hook had spent all those years prior to meeting his mom sailing the high seas. Hook put the anchor down so that Henry and him could have their own little pirate feast. Hook wanted to build a relationship with his son, even if the relationship only existed from his marriage. "Henry do you consider me to be a father-figure to you?" "Of course Hook. You were there for me when my birth-father died, and you've been there for my mom and I ever since. Of course you're my father." Hook smiled uncontrollably with happiness. He finally had a family. "So do you trust me with anything? I just want to be there for you now, since I wasn't able to be there the first 12 years of your life." Henry felt this would be a great time for questions that he really needed answers to. He had only really had mom-figures in his life, so he hadn't really felt comfortable to talk about anything related to 'the puberty talk'. "Uhh.... Can I ask you a question about... well.. our bodies?" Hook chuckled at Henry's nervousness. Hook himself was once self conscious about his body, so sitting in front of Henry now was like looking at a younger version of himself. "Of course Henry. I'm here to answer any questions. What did you have in mind?" "Well it's just.. David and I went to the beach while you and Mom were away.." Henry was not going to tell Hook that he had lost his virginity to David "..and I couldn't help but notice that when he was shirtless and only wearing a pair of boxers that he was just bare skin with no hair, whereas you have chest hair that I can see despite you being fully clothed. I guess I just want to know, if I choose to keep growing my body hair out like you instead of shaving everyday like Grandpa, what's my body going to look like, and will people still want to be with me? Unlike Violet." Hook was both shocked and proud of Henry for asking such a question. Body hair was certainly something he struggled with when he first started going through puberty. "Well Henry, body hair is nothing to be ashamed of. I mean, your mom loves me the way I am. I know your Grandpa likes to have no body hair, but that's just because back in the Enchanted Forest, King George made him manscape since he was a prince, and David just keeps at it to this day because it boosts his self-esteem and makes him feel like royalty, instead of just a Shepard's boy. It's a fetish of his if you will. But I'll show you what I look like if that put your nerves at ease." Hook began to take his necklace off and unbutton his shirt. Henry couldn't breathe. It was like a dream come true. Hook removed his leather jacket and his shirt, revealing his wonderfully built chest covered in his elegant brown chest hair. Killian continued to strip as he removed his shoes and socks. Halfway through untying his second shoe, Hook stopped and looked up at Henry and said "Lad you can go ahead and undress yourself as well. That way we can do a true comparison." Henry couldn't believe it. He thought he was dreaming. Henry slowing unbuttoned his shirt to reveal his slightly tanner skin after his beach session with David. When Killian starting to unzip his pants with his hook, Henry started to feel an erection coming on, and he knew he needed to stop it. He quickly thought back to all the bad things that had happened to him over the past two years, and just like magic, Henry's dick shrunk back down. Henry continued to unbutton his pants, and when he looked up, he noticed that both him and Hook were naked besides their boxers. Simultaneously, both men removed their boxers to reveal their beautiful cocks, and the delicious salty smell of their sweaty natural scents. They both made eye contact with each other after throwing their boxers to side of the ship, and then they just both started laughing. It was truly a father-son bonding moment. After they both were able to breathe again, Hook went over to stand directly to Henry's left, putting his thigh up against his. "Now Henry I noticed you got a tan from going to the beach with David. That is good because even though it's hard to tell under all my leg hair, my skin is actually the same shade as yours. So once you fully grown-in your leg hair, this is exactly what your legs will look like." Henry didn't know what came over him, but he went and felt Hook's thighs and calves. Henry stopped himself when he realized what he was doing and was quick to apologize. "It's quite alright lad. I know, it's tempting right? Just like petting a cat or dog. You can feel my abs too if you'd like. I see your starting to work on your six pack yourself." Henry was flattered that Killian was looking at him, and even more so surprised that Hook was okay with him doing this. Henry placed his hand on Killian's rock hard abs. To be able to feel such a furry pair of abs was unreal. He continued to move upward, grasping Hook's breasts and teasing his hairy nipples with his fingers. Finally he reached Killians spiky face, and caressed it. Hook chuckled "I know. It's weird right? How my hair is so soft everywhere else, but it's sharp and spiky on my face. Now I'll show you my arms." Hook gently grabbed Henry arm and placed it up against his, showing him yet another preview of his body hair to come. Hook went on to explain how he manscaped. "Now I'll admit, I do shave my upper arms, just so the hair itself doesn't take away from my guns. And now that your mom and I are together, she's offered to be my second hand and she helps me shave my back. Back hair doesn't bother me, but one day when you, David, and I can go to the beach to have a 'bro-day,' I'd rather not have that on me. Quite honestly, it's just not attractive to anyone. But I'll help you shave your back if you want me to, once yours starts growing in." Henry had to chuckle when Hook said he wanted a bro-day, but he also thought it was sweet. Henry went on to feel-up Hooks back. The skin on his back was almost as soft as his chest hair. Henry continued his descent down to Hook's ass. Henry asked "Do you mind if I..?" Hook smiled. "Of course not." Then Hook bent over the table so Henry could get a better look at Hook's hairy asshole. Henry's mouth watered at the sight of Hook's red cherry. Surrounded by his brown ass hair, it appeared to be a juicy donut display. Henry so badly wanted to just go right ahead and eat his asshole, but he didn't want to ruin his relationship with Killian. Hook stood up and then stood directly in front of Henry. "Now to show you what men are really self conscious about. Their pubic hair and dick size. Never let anyone tell you that having a bush down there is bad thing. The hair itself is great for rebound when having sex, and also is a great help in preventing STD's. And yes Henry, we did know what those were back in the Enchanted Forest. That's not just a modern day concept. Now to compare the difference between a man's and a teenager's penis.." Hook stepped closer to Henry and grabbed Henry's dick, holding Henry's and his own directly up against each other in his palm. Henry quickly thought about his dark past again to prevent an erection. He could not get hard, no matter the situation. Killian continued using his hook to show Henry what he was talking about "notice how I have a little bit of hair along my shaft. Right now yours is bare." Henry shuddered inside as Hook's cold traced carefully along his shaft. "Once you turn 16 or so, you'll start growing hair all way up to your head. Don't worry, the ladies don't mind." Killian's hook migrated its way up to the head of Henry's cock, and Henry couldn't hold out anymore. His dick became erect, and he moaned as it rubbed up against Killian's dick. To his surprise, Killian moaned as well, because as Henry's dick rubbed against his own, he himself grew an erection. Both of them moaned in unison, and stepped back to let the full length of their cocks expand outward as they rubbed against one another. Henry snapped back to reality and quickly stepped back and frantically apologized. The pirate just chuckled. "Henry it's alright. That's perfectly normal. I should've realized what I was doing was too physical. It would happen to anyone. I got a little carried away trying to give you a sex talk I guess." Both men, still hard, just looked at each other and laughed again. Henry still needed to ask something else "Hey um Killian, can I ask you something else while we're still having the sex talk?" "Sure lad. What else do you wanna know?" "Well it's just, I'm sure you know I've missed a lot of school since we've been traveling a lot, and I'm the author and everything. Now that I'm back at school, a lot of the boys have been talking about masturbation. That's nothing new for me, but everyone has starting talking about shooting cum and how far it goes. Mine just flows out and covers my hand when I do it. I was wondering if you could maybe show me what exactly they were talking about, since we're both hard now and all." Killian was speechless. He had never heard of anyone having contests about how far they could shoot their cum. He wanted to help Henry out and not make him feel self-conscious. "Sure lad. Why not? We've already made it this far. Now the reason they shoot farther than you is probably because at our young age, we tend to rush when we jack off because we don't want our parents walking in on us. When you're jacking off, you need to go slowly. Just like sex, the longer you go, the more enjoyable it is. Now I know you kids watch porn on that television thing of yours, but no matter how hot the porn you're watching or fantasies are, you cannot give in until you for sure cannot hold out any longer. Let me show you what I do to prolong my ejaculation." Killian removed his hook and hung it up on the wall so that he only had his handless arm. Henry didn't understand why he did that, since his hook had been quite the turn-on for Henry, but he didn't bother asking, as he was enjoying the show in front of him. Killian spit into his hand and rubbed it all over his glorious cock. Hook had already begun to sweat, and his wet chest hair had Henry's erect cock jumping for joy. Hook ran his handless arm across his chest. The skin had successfully grown back around Hook's wrist, but he did have a bump that was clearly one of his bones sticking out. He ran the tip of the bone over his nipple, and instantly Hook closed his eyes and moaned. That's when Henry lost it and sped over to eat Hook's now sweaty asshole. Hook moaned even louder, screaming in ecstasy and surprise. Hook didn't care that Henry was his son now. This felt FUCKING AMAZING. "Oh my god Henry! YES. Eat my ass like a pancake!" Henry had his whole tongue up Hook's ass, slurping like crazy, the sounds only made him harder. He began to slap his hairy ass, causing sweat to splatter on him. He tasted amazing, and Hook's scent was out of this world. Henry really wanted to feel Hook's prostate, but his tongue wasn't long enough. Henry took things to the next level and stuck his cock in the hairy pirates ass. The pirate released a moan that sent out such a pleasurable vibration up Henry's dick. They moaned in a singing unison. They had found their song, as Emma had before the final battle. Their song was duet, and this was where they were meant to be, penetrating and feeling up every inch of the others body. Henry continued the pound the pirates ass with his cock, simultaneously smacking his ass and licking his sweating hairless back. Hook yelled out to Henry "Henry! I'm going to cum! Watch how far I shoot!" Henry looked up and gave the pirate one last spank before a pure white rope shot halfway across the room, skillfully landing in Hook's drink. Henry froze "How did you do that?" Hook grinned. "It takes practice." Killian walked over to the table, picked up his drink, and took a sip. "You want some?" Henry did not hesisitate, and spastically went to drink the pirate's cum. Sweet with a hint of salty, the perfect combination. "Now it's your turn." Henry was confused "What do you mean?" "Well I'm going to teach how to shoot like me. After all, you need to cum after you just pounded my ass like a god, unless you want to get blue balls. And trust me nobody wants that." Henry didn't put up a fight. He'd developed a new fetish for being dominated by older men. "Now Henry, first I want you to place your hands on your breasts and massage them. Pinch your nipples from time to time. Trust me it'll feel amazing. Don't forget to hold out from ejaculating. If you need me to stop so you can control yourself, just slap your thigh and I'll know. Believe me I know how hard it is to find your words when you're at climax. You ready?" "Is that even a question?" The pirate smiled and went on to eat the boys ass and use his fingers to loosen him up. Henry's moans allowed the pirate to regain his erection. So he went right to it. Killian stood up, wrapped his hand around the boys cock, and stuck his ginormous cock up Henry's ass. Henry slapped his thigh, and Killian stopped with his dick fully inserted up his ass. "Henry does it hurt. I'm so sorry. We shouldn't be doing this." "NO. No I want to keep doing this. Your just on my prostate and I almost came." They both chuckled. Then Hook had an amazing idea. He took his hand off Henry's raging erection stuck then in Henry's as along with the full length of his thick cock. He dare not move his dick, for his plan didn't not involve him pleasuring Henry's prostrate. Not yet anyway. He continued putting more of his fingers in his ass one by one, whilst Henry slowed his breathing so he could hold off his ejaculation. Hook went on to lick up the boy's back and gently bite on his ears, releasing beautiful moans from Henry. Finally the pirate was able to fit all his fingers in the boy's ass along with his throbbing monster of a cock. He began to slowly pull his hand out of Henry's ass, and then his dick. Henry squealed in dismay, as he thought the pirate was done. But he wasn't. He had only just begun. Henry all of the sudden let out a moan that startled the birds above deck. Hook had stuck his handless arm up Henry's ass, with the bone of his arm directly massaging his prostate. Hook used his hand to jack off Henry. "Come on Henry, I know you have it in you. Make it all the way to that cup. Do it for Daddy." Henry lost it right there while screaming "YES DADDY!" And two thick ropes of cum were released from Henry's cock. The first shot all the way acrossed the room, splattering across Killian's hook he had hung on the wall. The second landed in Hook's drink to join Hook's last load. But Hook needed more, so he stuck his dick up Henry's ass once more. "It always feels amazing when someone continues to fuck you after you've cum, and then cum in your ass themselves." And he did. Hook warmed up Henry's ass by filling it with his cum, and drank it like a water fountain as it dripped out. Both men were out of breathe and took a minute to come back to reality. Killian went over and grabbed his hook, and lick Henry's cum off of it: "oh my god this taste so fucking good Henry." He let Henry lick his hook. "Mhmm that does taste good. What about both of them together?" Henry went over to the cup both him and Killian had ejaculated in. It was absolutely delicious, and he could believe what good of a combination him and Killian made. Literally. Then Henry made a realization "What did you mean you said it feels better when someone continues to fuck you after you cum? Have you done this before?" "Well um, you see lad..." Killian paused for a second before revealing his secret. "When I lost my first wife Milah, I was in a dark place. Shortly after I returned from Neverland. I gave up my quest of revenge and settled in an old pub and began to drink heavenly. So drunk that when your Grandfather and I met, I thought he was a girl because of his long hair. And he was so drunk he also thought I was a girl because of my guyliner. Long story short we had wonderful sex, the kind you only read about in fairytales. He actually still had all his body hair because then he was still a Shepard's boy, and He was actually my first time. Milah and I never had sex because we weren't planning to have kids during our pirate days, and we didn't have those things called condoms that this world has. David and I woke up the next day realizing what had happened, and he freaked. David realized he really was becoming a drunk like his father, so decided to stop and he never came back to the pub again. I like to think that our time together saved his life. Anyway, depressed that I had lost yet another partner, I went back down my path for revenge since I thought I had nothing to live for. Then when I came to Storybrooke, and found David, I knew it had to be fate. When you were kidnapped by Pan, and David and I were alone, we made love, and I got to see his new Prince body. Sadly, he once again hated me when I became conflicted with my physical attraction to him, but a romantic attraction to your mother. I mean who wouldn't be? It's screwed up, but what else is new in this world, am I right? After a year, when he saw that I was truly in love with your mother, he learned to overcome his feelings and accept me as his son. Now that he's my Daddy... Gosh that makes me hard... him and I are closer than ever. Close enough for him to me about your little beach session with him." Henry froze. "You knew?" Hook grinned. "That's right Henry. I knew. Your Grandpa was both your first time and my first time. I wasn't kidding when I said I wanted you, me, and your Grandpa to have a beach bro day together. He was right. You are a natural at sex. But now your can show David what I taught you today, and use your new stamina to your advantage next weekend." Henry stared confused "Next weekend?" "Yes Henry. Next weekend. We're finally having our LONG overdue bro-day. And something tells me that we're all going to be really burnt out afterwards. And not because of the sun." Henry and Hook both smiled. Hook led Henry over to his bed, and they laid down while Henry cuddled up and lay his head on Hook's soft hairy chest. They both felt safe, and most importantly, not alone. And next weekend, David would be able to share the feeling."

**Notes for the Chapter:**

> As always, if you have any suggestions or anything sex-related you would like to discuss, please email me at:  
> Bobgod1234@yahoo.com  
> ;)


	3. The Long-Awaited Reunion

Here's a Preview of What's to come in the Next Chapter ;) Any thoughts or kinks that you would like for me to add, please email me at Bobgod1234@yahoo.com

<https://www.flickr.com/photos/150271291@N07/shares/j96c90>

 


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